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When your prospect is about to initiate a trial of your product, one of the best ways to ask them about their buying process is to ask what happens afterward, assuming everything goes well: “Before we start the trial, assuming everyone comes back to you at the end of the trial with great feedback, what happens after that?” This a great, open ended question that will help you understand what the next steps are after a successful trial.

Curious what Gong.io data has to say about this, but I feel that saying ‘Sorry’ more often than not when selling is a good idea. I used to think it made you look weak, but it actually makes you more relatable, human, and empathetic. An email subject line example is: “Sorry Bob, is next week better for you to speak?” A phone example is: “Sorry if I may be mistaken about this, but…” People open up more. Use Sorry. You’ll feel more relatable.

Answering your prospects questions gives you the right to ask them questions. Timing of your questions and asking thoughtful questions are important, yet when you answer their questions, you’ve earned the right to ask. Answering their question is like catching the ball so-to-speak, then you wind up and throw the ball back, asking them a very thoughtful question. Just loading off question after question could come across as abrasive, when you instead want to come across as curious, and have a good “wind-up.” Curiosity will win the day on every call. In order to have a natural transition to ask a question back, some ‘curious’ phrases to use prior to asking your questions include “Out of curiosity,” “That reminds me,” Speaking of which,” “On that note,” “I was thinking about this before the call and wanted to learn more about,” “Curious to understand.” These help make your calls like conversations, instead of like an interview.

The following is a real life anecdote which represents some “out of the box” prospecting, resulting in actual meetings with senior level members of large firms. — My colleague, Daniel Berman, recently called a prospect and got the executive assistant, Jessica, on the phone. After speaking with Jessica, Dan subsequently sent the respective Managing Director an email with subject line “Spoke to Jessica,” a great way to get an email open — Lesson #1. The “out of the box” email read: “Hi Bob, Just spoke with Jessica and she mentioned you were busy right now. Would you have 5 minutes for a brief discussion later today or tomorrow on……..? I will personally show up to your office and let you punch me in the face if you find the call both uninteresting and a waste of your time.” — Now, this is clearly not your common way of expressing a meeting request, but it did end up in a firm-wide, introductory meeting. We’ve also tried the more “G rated” version: “You can dismiss us if you really feel it’s not relevant, but we’re quite confident it will not be a waste of your time.” This also resulted in scheduled meetings. Being somewhat self dismissive actually works — Lesson #2. Good lessons on being creative, and having fun in sales

Salespeople understand that the more we’re able to actually speak with our prospects instead of emailing them, the more productive it will be. John Barrows speaks about this specifically with regard to negotiation, yet it’s an important rule of thumb across all types of sales conversations, including next steps, feedback, value add messages during the sales cycle, etc. (excluding logistics). Question is, do we follow the same rule when speaking with our own colleagues? Are we busy slacking or emailing important conversations to the person that sits right next to us, or do we strive to have in-person and/or phone discussions instead? Yes, not all conversations require it, but the most relevant ones do. If it has a more positive outcome with our prospects, how much more so on our very own sales teams? This creates a much more pleasant environment, resulting in more sales! A rule of thumb, I try to choose these forms of communication in the following order (1) In person, (2) Phone, (3) Text, (4) Email. We should try and practice what we preach, and always seek to improve.

Christopher Voss in “Never Split The Difference” talks about how allowing prospects to say “no” makes them feel relaxed and protected, where having them trapped into ‘yes,’ makes them feel more pressured and uneasy. Thomas Freese in “Question Based Selling” also discusses how placing the negative into your questions rewards you with more honest and accurate responses from your prospect. Based on this great insight, if you do have the chance to speak with the decision maker, one question I like to ask at the very end of a demonstration call is, “Based on everything we spoke about, what would be a reason why we would NOT work together?” This not only indirectly implies to the prospect that you are ok with them telling you no, but because you are asking an honest question, which most people would not think to ask, you’ll find they’ll have absolutely no trouble telling you why. Now, you can know the truth, and deal with it sooner, before it’s too late.

Towards the end of a demo, your prospect may say something along the lines of, “This looks great, I just need to take this back to the team to get their thoughts.” When this comes up, a good question to ask is, “What hesitations do you anticipate might come up with the team?”

The prospect’s answer will usually reveal potential objections and because you asked this while still on the phone, you will have the opportunity to overcome them before they come up in the team meeting and arm your prospect (champion) with the best response. This can significantly improve the likelihood of the prospect being able to sell your solution internally.

If you don’t ask this question, you will hear about the hesitations after the meeting where you will be playing defense. This question can also reveal what the prospects own hesitations might be and will give you an opportunity to address them while you still have the time on the call.

I mentioned in a previous post that open ended questions are the best to ask. However, they don’t just apply to very big asks, but are just as relevant for the small asks. One powerful example is, when conducting a demo, instead of asking ‘Do you have any questions for me at this point?,’ (a close ended question) it’s way more effective to say ‘So, what questions might you have for me?’ This accomplishes two things: (1) It implies that anyone taking this seriously should actually have real questions for you. (2) It allows the prospect to actually think of something to ask, instead of wondering whether or not they even have a question in the first place. It works!!

During a demo, you’ll hear a lot of sales people asking close ended questions like (1) ‘Do you find this tool helpful?’ Or (2) ‘Do you think you would use something like this?’ Although you can still get a sale from asking these types of questions (assuming people actually find value in your product), these questions are not nearly as strong nor as powerful as open ended questions. As an example, I’d replace question (1) with ‘How does this compare to your current process?’ I’d replace question (2) with ‘Where do you think this could fit within your process?’ More thoughtful, open ended questions call for genuine conversation, allowing the prospect to actually sell themselves!

Great sales people ask thought provoking questions. However, thought provoking questions are the toughest to ask. They just make you downright uncomfortable. Solution? Cushion the question! Cushioning is opening and closing the question with a soft statement, re-framing the ‘tough’ question into a ‘soft’ ask. For example, first open with something like “Out of mere curiosity…” or “This may be a bit premature to ask, but…” followed by your ‘tough’ question. Immediately after that, close it with another cushion, such as “Thought it was worth picking your brain about it,” or “Just looking to see what it’s like to be in your shoes.” You’ll be pleasantly surprised to see those ‘tough’ questions being answered quite comfortably.